90-04-0 Usage
Description
o-Anisidine, also known as 2-methoxyaniline, is an organic compound that serves as a chemical intermediate in the production of various products. It is an aromatic amine with the chemical formula C7H9NO and is known for its potential health risks, including causing methemoglobinemia and cancer in humans.
Uses
Used in Chemical Industry:
o-Anisidine is used as a chemical intermediate for the production of pigments, dyes, pharmaceuticals, and fragrances. It plays a crucial role in the synthesis of numerous azo and triphenylmethane dyes and pigments, such as C.I. direct red 72, disperse orange 29, direct yellow 44, direct red 24, and acid red 4.
Used in Pharmaceutical Industry:
o-Anisidine hydrochloride is used as a chemical intermediate in the production of pharmaceuticals, including the expectorant guaiacol. It aids in the development of medications that help relieve respiratory issues.
Used in Steel Industry:
o-Anisidine serves as a corrosion inhibitor for steel, protecting it from rust and other forms of corrosion. This application extends the lifespan of steel structures and equipment.
Used in Polymer Industry:
o-Anisidine is used as an antioxidant for polymercaptan resins, enhancing their stability and performance in various applications.
Synthesis Reference(s)
Tetrahedron Letters, 24, p. 4733, 1983 DOI: 10.1016/S0040-4039(00)86242-5
Air & Water Reactions
o-Anisidine darkens on exposure to air. Insoluble in water.
Reactivity Profile
o-Anisidine is sensitive to heat. o-Anisidine is also sensitive to exposure to light. o-Anisidine is incompatible with strong oxidizers. o-Anisidine is also incompatible with acids, acid chlorides, acid anhydrides and chloroformates. o-Anisidine will attack some forms of plastics, rubber and coatings. .
Hazard
Strong irritant. Toxic when absorbed
through the skin. Possible carcinogen.
Health Hazard
o-Anisidine was carcinogenic in
experimental animals.
Fire Hazard
o-Anisidine is combustible.
Safety Profile
Confirmed carcinogen.
Moderately toxic by ingestion. Mutation data
reported. When heated to decomposition it
emits toxic fumes of NOx.
Environmental fate
Biological. o-Anisidine should be biodegradable according to OECD guidelines (Brown and
Labouerer (1983).
Chemical/Physical. At influent concentrations (pH 3.0) of 10, 1.0, 0.1, and 0.01 mg/L, the GAC
adsorption capacities were 52, 20, 7.8, and 3.0 mg/g, respectively. At pHs 7 and 9, the GAC
adsorption capacities were 110, 50, 23, and 10 mg/g at influent concentrations of 10, 1.0, 0.1, and
0.01 mg/L, respectively (Dobbs and Cohen, 1980).
Purification Methods
It is separated from the m-and p-isomers by steam distillation. It is also separated from its usual synthetic precursor o-nitroanisole by dissolving it in dilute HCl (pH <2.0) extracting the nitro impurity with Et2O, adjusting the pH to ~8.0 with NaOH, extracting the amine into Et2O or steam distilling. Extract the distillate with Et2O, dry the extract (Na2SO4), filter, evaporate and fractionate the residual oil. Protect the almost colourless oil from light which turns it yellow in color. [Biggs & Robinson J Chem Soc 3881961, Nodzu et al. Yakugaku Zasshi (J Pharm Soc Japan) 71 713, 715 1951, Beilstein 13 IV 806.]
Toxicity evaluation
It is primarily metabolized by cytochrome P450 isozymes, and
it forms two o-anisidine–DNA adducts with DNA. It causes
DNA damage by a metabolite in the presence of metals such
as Cu(II). It can also cause Cu(II)-mediated oxidative DNA
damage.
Check Digit Verification of cas no
The CAS Registry Mumber 90-04-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 0 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 90-04:
(4*9)+(3*0)+(2*0)+(1*4)=40
40 % 10 = 0
So 90-04-0 is a valid CAS Registry Number.
90-04-0Relevant articles and documents
Rat liver microsomal metabolism of o-aminophenol and N-(2-methoxyphenyl) hydroxylamine, two metabolites of the environmental pollutant and carcinogen o-anisidine in humans
Naiman, Karel,Hodek, Petr,Liberda, Jiri,Schmeiser, Heinz H.,Frei, Eva,Stiborova, Marie
, p. 1229 - 1247 (2010)
o-Aminophenol and N-(2-methoxyphenyl)hydroxylamine are human metabolites of the industrial and environmental pollutant and bladder carcinogen 2-methoxyaniline (o-anisidine). The latter one is also a human metabolite of another pollutant and bladder carcinogen, 2-methoxynitrobenzene (o-nitroanisole). Here, we investigated the ability of rat hepatic microsomes to metabolize these metabolites. N-(2-methoxyphenyl)hydroxylamine is metabolized by rat hepatic microsomes to o-aminophenol and predominantly o-anisidine, the parent carcinogen from which N-(2-methoxyphenyl)hydroxylamine is formed. In addition, two N-(2-methoxyphenyl)hydroxylamine metabolites, whose exact structures have not been identified as yet, were generated. On the contrary, no metabolites were found to be formed from o-aminophenol by rat hepatic microsomes. Whereas N-(2-methoxyphenyl)hydroxylamine is responsible for formation of three deoxyguanosine adducts in DNA, o-aminophenol seems to be a detoxication metabolite of N-(2-methoxyphenyl)hydroxylamine and/or a parental carcinogen, o-anisidine; no o-aminophenol-derived DNA adducts were found after its reaction with microsomal cytochromes P450 and peroxidases.
Pt nanoparticles entrapped in ordered mesoporous carbons: An efficient catalyst for the liquid-phase hydrogenation of nitrobenzene and its derivatives
Li, Junrui,Li, Xiaohong,Ding, Yue,Wu, Peng
, p. 1995 - 2003 (2015)
Pt nanoparticles entrapped in ordered mesoporous CMK-3 carbons with p6mm symmetry were prepared using a facile impregnation method, and the resulting materials were characterized using X-ray diffraction spectroscopy, N2 adsorption-desorption, s
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Brand,Kranz
, p. 154 (1927)
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DMF-Assisted Radical Cyclization of o-Isocyanodiaryl Ethers via 1,5-Aryl Migration: Construction of 2-Arylbenzoxazoles
Cai, Jingyu,Ding, Qiuping,Peng, Yiyuan,Song, Zhibin,Tan, Yuxing,Ye, Xiaoling,Yuan, Sitian
, p. 1485 - 1492 (2022/01/20)
A novel DMF-assisted radical cyclization of o-isocyanodiaryl ethers via 1,5-aryl migration has been developed for the synthesis of a series of 2-arylbenzoxazoles by the FeCl3/TBHP/Et3N catalytic system in DMF. However, N,N-dimethylbenzo[d]thiazole-2-carboxamide and N,N-dimethylbenzo[d]selenazole-2-carboxamide were obtained from the corresponding substrate 2-isocyanophenyl p-methoxyphenyl thioether and 2-isocyanodiphenyl selenoether under the same conditions. A possible mechanism may involve aryl 1,5-migration and DMF-assisted radical cyclization of o-isocyanodiaryl ethers.
A Concise Route to Cyclic Amines from Nitroarenes and Ketoacids under Iron-Catalyzed Hydrosilylation Conditions
Ammaiyappan, Yuvaraj,Darcel, Christophe,Tongdee, Satawat,Wu, Jiajun
, p. 3859 - 3865 (2021/07/12)
Starting from nitroarenes, under hydrosilylation conditions, using a well-defined N-heterocyclic carbene iron(0) catalyst, (IMes)Fe(CO)4, the corresponding aniline derivatives were produced in 61–92% isolated yields. More impressively, a selective synthesis of cyclic amines such as pyrrolidines, piperidines and azepanes were conducted from levulinic acid, 1,5- and 1,6-keto acids, respectively. The sequential procedure proceeded under both visible light irradiation and thermal conditions with 20 examples in isolated yields up to 69%. (Figure presented.).